HCID 899189, compound → 856047-84-2

HRID 2283209Notes

Reaction equation

HRID 2283209 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:6])[CH3:2]>C1COCC1.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][N:3]([CH2:17][CH3:18])[CH2:1][CH3:2])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 899189HCID 899189, compound

Product 1

HCID 16779355856047-84-2

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(Diethylamino)-N-(3-nitrophenyl)acetamide 4 (0.73 g, 2.90 mmol) was dissolved in anhydrous THF (20 ml) under an atmosphere of N2, then Pd/C (0.073 g) was added. The atmosphere was then saturated with H2 and the mixture stirred overnight. The crude product was filtered through celite, the celite washed with EtOAc and the organic solution evaporated in vacuo. The crude was dissolved in DCM (75 ml), washed 3 times with 5N aqueous NH4OH solution (50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. Compound N-(3-aminophenyl)-2-(diethylamino)acetamide 5 was obtained as a yellow oil (0.58 g, 90%) without requiring any further purification; Rf 0.44 [5% MeOH in DCM]; δH (CDCl3, 400 MHz) 9.28 (1H, s, NH), 7.26-7.20 (1H, m, ArH), 7.07 (1H, t, J=8.0 Hz, ArH), 6.74-6.72 (1H, m, ArH), 6.43-6.40 (1H, m, ArH), 3.71 (2H, broad s, NH2), 3.11 (2H, s, CH2), 2.65-2.59 (4H, m, 2×CH2), 1.69 (6H, t, J=7.2 Hz, 2×CH3); δC (CDCl3, 100 MHz) 169.95 (C═O), 147.27 (Ar—C), 138.64 (Ar—C), 129.61 (Ar—CH), 110.74 (Ar—CH), 109.17 (Ar—CH), 105.92 (Ar—CH), 58.14 (CH2), 48.79 (2×CH2), 12.39 (2×CH3); HRMS m/z calc. C12H20N3O [M+H]+222.1601. found [M+H]+ 222.1694.

Workup

  1. filtrationThe crude product was filtered through celite
  2. washthe celite washed with EtOAc
  3. customthe organic solution evaporated in vacuo
  4. dissolutionThe crude was dissolved in DCM (75 ml)
  5. washwashed 3 times with 5N aqueous NH4OH solution (50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-4c4f81abfa244871aa3c821d7cc3295b
Source dataset
uspto-grants-2015_09
Patent number
US09145377B2

Reaction notes

Loading…